Synthesis, Antibacterial, and Antifungal Evaluation of Some New Quinazolinone-Azole Hybrids

Abstract

Nowadays, the need to replace the existing drugs is felt more than ever by increasing drug resistance. Quinazoline is one of the major heterocyclic compounds in biological activity. This research was done to synthesize new derivatives of quinazolin-4(3H)-one and evaluation of their antibacterial and antifungal properties. Ten new quinazolin-4(3H)-one derivatives (5(a–d), 6(a–d), and 7(a,b)) were synthesized by using the nucleophilic substitution reaction of 2-(chloromethyl)-3-(4-chlorophenyl) quinazolin-4(3H)-one (4) and the heterocyclic moieties of 1,3,4-oxadiazole I(a–d) or 1,2,4-triazole (II(a–d), III(a,b)) in the presence of potassium carbonate as base and in acetone as solvent. The chemical structures of the products were approved using 1H-NMR, 13 C-NMR, IR, and Mass spectroscopy. The antimicrobial activity of the compounds was assessed against a panel of Gram-positive and Gram-negative bacteria and species of Candida and Aspergillus fungal. Minimum inhibitory concentration (MIC), minimum bactericidal/fungicidal concentration (MBC/MFC), and inhibition zone (IZ) of these compounds were determined. As results shown, 7a showed better effects against Staphylococcus epidermidis, Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa than the other compounds. However, 5d showed better effects against Proteus vulgaris. Compound 6b showed better effects against Candida albicans, Aspergillus fumigatus, and Aspergillus niger, also compound 5a showed better effects against Candida glabrata.